Transcript Natural Products Chemistry

Natural Products Chemistry
Amir E. Wahba, Ph.D.
Assistant Professor of Natural Products
Chemistry Department
Faculty of Science, Damietta University
Instructor
• Dr. Amir E. Wahba
• Research Interest:
• Marine natural products, total synthesis of natural products, cancer
chemotherapy, pseudo LDL nanoparticles for targeted delivery of cancer
chemotherapy
• Contact:
• Office hours: Saturday, by appointment
• Email: [email protected]
What Are Natural Products?
What Are Natural Products?
What are Natural Products?
• Living organisms produces natural products for several reasons:
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Live
Grow
Reproduce
Defense
Communicate
• Examples of living organisms that produces natural products:
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Bacteria
Fungi
Plants
Marine organisms (sponges, alga...etc)
How Do plants produces chemicals?
Biosynthesis
• Primary Metabolism: All the chemical reactions necessary for the live
of the organism by itself.
• Primary Metabolites: All the chemical products involved in the
Primary Metabolism.
• Secondary Metabolites: All the chemical products that are produced
by the living organism but are NOT involved in the primary
metabolism. Not necessary for the live of the organism by itself but
useful for interaction with others (chemical communication, chemical
defenses).
Biosynthesis: Building Blocks
• Tetrahydrocannabinol
• Moderate analgesic
Terpenes
• Volatile oily compounds
• Usually give the smells of plants
• Essential oils
• All aliphatic compounds
• Biosynthetically obtained from isoprene unit
Terpenes: Classification
Number of carbon atoms
10
15
20
25
30
40
>40
Class
Monoterpenoids (C10H16)
Sesquiterpenoids (C15H24)
Diterpenoids (C20H32)
Sesterterpenoids (C25H40)
Triterpenoids (C30H48)
Tetraterpenoids (Carotenoids)
(C40H64)
Polyterpenoids
Terpenes: Isoprene Rule
• Isoprene rule:
Monoterpenoids and Sesquiterpenoids
• Isolation:
• Steam distillation
• Extraction with volatile solvents
• Structure Elucidation:
• Pure sample
• Molecular formula
• Mass spectrophotometer
• Chemical reactions
• Complete Structure:
• Chemical methods
• Modern Spectroscopy (IR, NMR, 2D-NMR)
Myrcene
• Acyclic monoterpenoid hydrocarbon
• Isolated from verbena and bay oils (‫)ورق الغار أو ورق موسى‬
• Used in perfume industry and as flavoring material in cooking
• Molecular formula: C10H16
General Chemical Methods
• Catalytic hydrogenation:
• Ozonolysis
Structure Elucidation of Myrcene
Structure Elucidation of Myrcene
Citral
• 60-80% in lemon grass oil
• Smell of lemons
• Molecular formula: C10H16O
Citral: Structure Elucidation
laevulic acid
Citral: Structure Elucidation
• Expected questions:
• Building blocks for the biosynthesis of natural products
• A chemical puzzle that describe the structure elucidation of a terpenoid